Dimethylamine → Methyl 3-cyano-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-bromo-2-methylbenzoate (0.646 g, 2.8 mmol) in 4 ml of dimethylamine was added Pd(OAc)2 (0.5 mol %), sodium carbonate (0.3 g, 2.8 mmol), K4[Fe(CN)6].3H2O (0.262 g, 0.62 mmol). The mixture was heated to 120° C. and stirred at this temperature for 4 hours then at RT for 18 hours. The reaction mixture was diluted with 30 ml of ethyl acetate and the resulting slurry was filtered through Celite. The filtrate was washed with water (2×15 ml) then 5% aqueous ammonium hydroxide (1×15 ml). The organic layer was dried over anhydrous sodium sulfate then filtered and concentrated to provide methyl 3-cyano-2-methylbenzoate (0.248 g, 50% yield) (S. Weissman, D. Zewge, C. Chen, J. Org. Chem. 2005, 70, 1508-1510). 1H-NMR (400 MHz, DMSO-d6): 8.09 (d, 1H), 8.04 (d, 1H), 7.53 (t, 1H), 3.87 (s, 3H), 2.66 (s, 3H).

Provenance & Evidence